It’s getting closer and closer to Halloween and it seems to be getting warmer here in Texas… alas, most likely no cool holiday here! I guess I can pretend – especially with these homemade Oreos.

On the subject of Oreos themselves, I’m sure you have some who are goo goo over the things and some who are just “eh”. Me? I’m somewhere in between. I like oreos (really liked them as a kid – you know, you take it apart and lick the crème filling off?) but am not utterly tempted by them.

These homemade Oreos however, are a different story. I first tried a homemade Oreo at a local bakery in Dallas – Creme de la Cookie – and fell in love. But then came the chocolate covered ones… it was love at first bite.

So of course some attempts were made to make some at home that tasted just as good, but none ever tasted exactly like the ones from Creme de la Cookie. Then one day, my sister found out that what they were using as the cookie part was chocolate shortbread – ah ha! The secret comes out… :)

This was all a couple of years ago but I hadn’t forgotten, so when I decided to make my own homemade Oreos it was certain the cookies were going to be chocolate shortbread. But um, doesn’t that kind defeat the whole Oreo thing? I don’t know, does it? All I know is that these chocolate sandwich cookies were delicious, far, far better than any Oreo you will ever taste, and I wish I had more!

The cookies taste awesome on their own, but coating them in semisweet chocolate just takes them to a whole new level.

The lowdown: Halloween themed chocolate sandwich cookies with a crème filling dipped in semisweet chocolate. For extra fun, make them into cookie pops as pictured!

In a medium bowl, sift together the flour, cocoa powder, and salt. Set aside.

In the bowl of a stand mixer (or a large bowl using a hand mixer), cream together the butter and sugar until light and fluffy, about 3 minutes. Mix in vanilla extract. Slowly add in flour mixture and mix until combined. Between two sheets of waxed paper, roll the dough 1/4-inch thick as evenly as possible.

Chill for 30 minutes (I left mine in there longer, but only because I waited until later that afternoon to finish the rest of the process).

Position a rack in the middle of the oven and preheat the oven to 350° F. Line a large baking sheet with a Silpat baking mat or parchment paper.

Cut out the cookies with a cookie cutter (the one I used was 2 in. round) Arrange the cookies on the prepared baking sheet.

Bake for 15 minutes (one batch I cooked a minute or two less), or until crisp and firm. Let the cookies cool on the baking sheet for two minutes and then transfer to a wire rack to cool completely.

When cookies are cool, make the crème filling.

For the crème fillingIn a large bowl, combine butter, half and half, vanilla, and salt until well incorporated. Mixture will be lumping so scrape often.

Add the powdered sugar, scraping often and mix on low speed until well incorporated. Mixture will be a bit stiffer than cake icing. You may need to add slightly more half and half, but only slightly – remember, the crème is going to be thicker than most frosting. Mix in orange food coloring (see note below), if using.

Once incorporated, transfer mixture into a piping bag (or Ziploc bag with a small corner snipped off) if making a large batch of cookies. If you are halving the recipe, it is just as easy to use a small offset spatula.

Pipe or spread desired amount of filling onto one cookie and gently press another cookie on top to spread filling. Once all cookies are filled, melt chocolate.

Using a fork, dip cookies in chocolate and gently tap the fork (with cookie on it) on the bowl to shake off excess chocolate. Top with sprinkles, if desired.

Yields: about 2 dozen Oreos

Recipe Notes

Always remember that cookies continue to bake right out of the oven, so even if they haven't totally firmed up yet, take them out anyway – don't bake longer than necessary!
I used two different crème filling recipes – the one I'm giving you is from momables.com and is more like a buttercream but is totally delicious. However, if you want more of an Oreo effect, then go with the one (link below the recipe card) from Sally's Baking Addiction – it was good too!
The original recipe for the crème filling says: "You can freeze the extra filling for later use if need be. Just pop in a ziploc bag and bring to room temperature naturally when ready to use. Or save it in a glass jar up to 30 days in fridge."
Regarding the food coloring, I think I used about 3-4 drops but you can customize this to get the color you want. The color I got was somewhat of a light orange.